Water → 6-bromo-3,4-dihydro-1H-2lambda6,1-benzothiazine-2,2-dione

HRID 58861ノート

反応式

HRID 58861 の反応式
C1C(=O)N([Br:8])C(=O)C1.[NH:9]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[CH2:12][CH2:11][S:10]1(=[O:20])=[O:19].O.CCOC(C)=O>CN(C=O)C>[Br:8][C:17]1[CH:16]=[CH:15][C:14]2[NH:9][S:10](=[O:19])(=[O:20])[CH2:11][CH2:12][C:13]=2[CH:18]=1

参加物

6

反応物 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 122033353192-06-1

生成物 1

HCID 691080756-bromo-3,4-dihydro-1H-2lambda6,1-benzothiazine-2,2-dione収率 79.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

NBS (1.5 g, 8.2 mmol) was added to a solution of 3,4-dihydro-1H-benzo[c][1,2]thiazine 2,2-dioxide (1.5 g, 8.2 mmol) in DMF (15 mL). The reaction mixture was stirred overnight at ambient temperature followed by addition of water (200 mL) and EtOAc (100 mL). The two layers were separated and the aqueous phase was extracted with EtOAc (100 mL×3). The combined organic phases were washed with brine (200 mL×3), dried over anhydrous sodium sulfate, and concentrated. The residue was purified by flash column chromatography on silica gel (EtOAc/hexane=1:3) to afford 6-bromo-3,4-dihydro-1H-benzo[c][1,2]thiazine 2,2-dioxide (1.7 g, 79% yield).

後処理

  1. customThe two layers were separated
  2. extractionthe aqueous phase was extracted with EtOAc (100 mL×3)
  3. washThe combined organic phases were washed with brine (200 mL×3)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography on silica gel (EtOAc/hexane=1:3)

出典と根拠

ORDレコード
ord-c88953e3d60947be945fb965a6c5a488
出典データセット
uspto-grants-2016_09
特許番号
US09434761B2

反応ノート

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